New England is the birthplace of America – something remembered by Boston’s revolutionary sights, the grand manors of the Berkshires and the maritime heritage of Connecticut. But, spanning all six states, this curated road trip showcases so much more. Coastal drives and forest loops will see you between national-park islands, Maine lobster shacks and great forested mountains to end with beach-clad Cape Cod’s whales and fishing villages. It’s all brought together with stays in hand-picked hotels.
Days 1-2: UK/Boston
From the comfort of your included VIP airport lounge, you’ll board a day flight to Boston, where you’ll make your way to your hotel. While our Deluxe option is especially inviting for its early-20th-century good looks, both are centrally located, with all of the city’s delights on their doorstep. Wandering the cobblestone streets of the Massachusetts capital will bring you between historic sights that chart the American Revolution, from redbrick churches to timber tall ships. That’s without mentioning the leafy Harvard campus in Cambridge, the boutiques of Newbury Street and the pretty narrow lanes that wind through the townhouses of Beacon Hill.
Stay: Courtyard Boston Downtown (Standard) Fairmont Copley Plaza (Deluxe)
Day 3: Kennebunkport
Collecting your hire car, you’ll travel north along the New Hampshire coast, passing cragged bays to arrive into Maine. Then, after perhaps pausing at Portsmouth’s tree-lined streets and 18th-century colonial buildings, you’ll arrive into Kennebunk. As one of Maine’s prettiest seaport villages, it’s a favourite among the East Coast elite – something evident across elegant sea-facing mansions. George HW Bush even has a home here, while its pretty beaches offer further reason to linger. Both of our hotel options here are perched idyllically on by the water.
Stay: Nonantum Resort (Standard) The Boathouse Waterfront Hotel (Superior)
Days 4-5: Bar Harbor
Continuing north, you’ll sweep along the coast to Mount Desert Island. Home to Acadia National Park, it’s a region of sparkling lakes and old-growth forests that form the backdrop to serene hikes and kayak trips. We also highly recommend the drive up to the top of Cadillac Mountain. As one of the highest points on the eastern seaboard, it offers some truly majestic views. Your base for your two nights here is Bar Harbor, where weatherboard houses sit side by side with cute cafés that spill out onto the streets. It’s all fronted by glistening Frenchman Bay – a view showcased by both of our traditional-hotel recommendations.
Stay: Atlantic Oceanside Hotel (Standard) Harborside Hotel, Spa & Marina (Superior)
Days 6-7: Bretton Woods
Heading inland today, you’ll plunge through forests, dart across rivers and trace lake outlines to arrive into New Hampshire’s White Mountains. Here, hikes and skiing trails make the most of these New-England icons, while scenic drives bring you atop Mt. Washington and along the White Mountains Trail. This scenic byway sees you between cave gorges, scenic overlooks and waterfall-troubled chasms. In terms of accommodation, our Deluxe alternative is a special highlight – a 1902 Spanish-revival icon set right in the park itself. It’s played host to literary greats and past presidents alike.
Stay: North Conway Grand Hotel (Standard) Omni Mount Washington Resort (Deluxe)
Day 8: Woodstock
Travelling along the Kancamagus Highway – a former Indian trail that cuts through the White Mountains National Forest – you’ll continue on through dense woodland, famed for its autumn foliage. You’ll first arrive at the idyllic Lakes District, its glassy waters and golden fields pointing towards Vermont. Your home for the night will be Woodstock, a pretty village set among rolling countryside. Here, grand houses, churches and an oval green remember its 18th-century roots as the dignified seat of Windsor County.
Stay: 506 on the River (Superior) or Woodstock Inn & Resort (Superior)
Days 9-10: The Berkshires
Today, we highly recommend a visit to next-door Quechee Village to take in its glacial ravine – a Grand Canyon in miniature. It’s then on to Massachusetts and the Berkshire Hills. Long a green lung for New York’s moneyed, there are plenty of opportunities for hikes and stops at farm-to-table restaurants. Hancock Shaker Village is a special highlight for its 18th-century heritage. Your base for it all is charming Lenox. Often termed the ‘cultural heart of the Berkshires’, it impresses with grand houses and summer performances by the world-class Boston Symphony Orchestra. The mountain views from your accommodation are just as impressive, complemented by spa treatments and rounds of golf in our Deluxe option.
Stay: Briarcliff Motel (Standard) The Inn on Boltwood (Superior)
Day 11: Mystic
Heading into Connecticut, you’ll arrive back at the coast with Mystic. From its humble, 17th-century beginnings it grew into one of the greatest shipbuilding ports of the East Coast, churning out clippers, gunboats and naval ships throughout the 1800s. It’s a storied history that lives on to this day in the superb Mystic Seaport Museum. As America’s leading maritime exhibition, it’s a true step back in time, complete with everything from historic villages to working shipyards. You’ll contrast it all with the contemporary sleek of your hotel.
Stay: Hilton Mystic (Superior)
Day 12: Newport
Hopping south into Rhode Island, you’ll arrive into Newport – the summer resort of America’s first millionaires. Be sure to take a stroll along Ten Mile Drive to appreciate its stunning mansions, several of which are open for tours. Rough Point is a special favourite – a spectacular ocean estate of heiress and art collector, Doris Duke. Then, there’s the town’s colonial architecture, the pretty Cliff Walk and what’s believed to be America's oldest pub before you end the night in your cosy accommodation.
Stay: Newport Beach Hotel & Suites (Standard) Hotel Viking (Superior)
This trip has no fixed departures but restrictions may apply - check operator website
** If you see this next to a price, a specific price in your currency has not been provided, this is an estimated-only price based on a currency conversion, the price you pay may be different to that shown
Sign up to our weekly Trip Finder email and get a selection of the best trips to feed your Wanderlust